{3-[{4-[Bis-(3-tert-butoxycarbonylamino-propyl)-amino]-6-chloro-[1,3,5]triazin-2-yl}-(3-tert-butoxycarbonylamino-propyl)-amino]-propyl}-carbamic acid tert-butyl ester | 760976-96-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 三嗪类
• 英文名称: {3-[{4-[Bis-(3-tert-butoxycarbonylamino-propyl)-amino]-6-chloro-[1,3,5]triazin-2-yl}-(3-tert-butoxycarbonylamino-propyl)-amino]-propyl}-carbamic acid tert-butyl ester
• 英文别名: tert-butyl N-[3-[[4-[bis[3-[(2-methylpropan-2-yl)oxycarbonylamino]propyl]amino]-6-chloro-1,3,5-triazin-2-yl]-[3-[(2-methylpropan-2-yl)oxycarbonylamino]propyl]amino]propyl]carbamate
• CAS: 760976-96-3
• 化学式: C₃₅H₆₄ClN₉O₈
• 分子量: 774.402
• InChiKey: JJOQZIMYIUYOQK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.1
• 重原子数：
  53
• 可旋转键数：
  26
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  199
• 氢给体数：
  4
• 氢受体数：
  13

反应信息

• 作为反应物：
  描述：

  (R)-3-氨基吡咯烷 、 {3-[{4-[Bis-(3-tert-butoxycarbonylamino-propyl)-amino]-6-chloro-[1,3,5]triazin-2-yl}-(3-tert-butoxycarbonylamino-propyl)-amino]-propyl}-carbamic acid tert-butyl ester 以 四氢呋喃 为溶剂， 以94.5%的产率得到tetra-tert-butyl (((6-(3-aminopyrrolidin-1-yl)-1,3,5-triazine-2,4-diyl)bis(azanetriyl))tetrakis(propane-3,1-diyl))(R)-tetracarbamate
  参考文献：
  名称：

  Identification of diamine linkers with differing reactivity and their application in the synthesis of melamine dendrimers

  摘要：

  Diamine linkers for the synthesis of dendrimers based on melamine were identified using competition reactions. The relative reactivity of the surveyed cyclic monoamines varies by 40 times, expanding the previously identified series to an overall relative reactivity range of 320 times. Azetidine is 40 times more reactive than the cyclic, nine-membered ring (C8H17N), and 320 times more reactive than benzylamine. Reactivity differences are attributed to pK(a), values and sterics. Diamines incorporating these groups are useful linkers that can be employed in dendrimer synthesis. Specifically, the nucleophilicity of the individual amine groups comprising 3-aminoazetidine, 3-aminopyrrolidine, and 4-aminopiperidine varies by 100 times, 70 times, and 20 times, respectively. These linkers are incorporated into a generation three dendrimer. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2007.12.056
• 作为产物：
  描述：

  3,3'-二氨基二丙基胺 在 三乙胺 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 氯仿 为溶剂， 反应 2.0h， 生成 {3-[{4-[Bis-(3-tert-butoxycarbonylamino-propyl)-amino]-6-chloro-[1,3,5]triazin-2-yl}-(3-tert-butoxycarbonylamino-propyl)-amino]-propyl}-carbamic acid tert-butyl ester
  参考文献：
  名称：

  Cytotoxicity, Hemolysis, and Acute in Vivo Toxicity of Dendrimers Based on Melamine, Candidate Vehicles for Drug Delivery

  摘要：

  A small library of dendrimers was prepared from a common precursor that is available in 5 g scale in five linear steps at 56% overall yield. The precursor is a generation three dendrimer that displays 48 peripheral sites by incorporating AB(4) surface groups. Manipulation of these sites provided six dendrimers that vary in the chemistry of the surface group (amine, guanidine, carboxylate, sulfonate, phosphonate, and PEGylated) that were evaluated for hemolytic potential and cytotoxicity. Cationic dendrimers were found to be more cytotoxic and hemolytic than anionic or PEGylated dendrimers. The PEGylated dendrimer was evaluated for acute toxicity in vivo. No toxicity-neither mortality nor abnormal blood chemistry based on blood urea nitrogen levels or alanine transaminase activity-was observed in doses up to 2.56 g/kg ip and 1.28 g/kg iv.

  DOI：

  10.1021/ja048548j

文献信息

• Cytotoxicity, Hemolysis, and Acute in Vivo Toxicity of Dendrimers Based on Melamine, Candidate Vehicles for Drug Delivery
  作者：Hui-Ting Chen、Michael F. Neerman、Alan R. Parrish、Eric E. Simanek

  DOI：10.1021/ja048548j

  日期：2004.8.1

  A small library of dendrimers was prepared from a common precursor that is available in 5 g scale in five linear steps at 56% overall yield. The precursor is a generation three dendrimer that displays 48 peripheral sites by incorporating AB(4) surface groups. Manipulation of these sites provided six dendrimers that vary in the chemistry of the surface group (amine, guanidine, carboxylate, sulfonate, phosphonate, and PEGylated) that were evaluated for hemolytic potential and cytotoxicity. Cationic dendrimers were found to be more cytotoxic and hemolytic than anionic or PEGylated dendrimers. The PEGylated dendrimer was evaluated for acute toxicity in vivo. No toxicity-neither mortality nor abnormal blood chemistry based on blood urea nitrogen levels or alanine transaminase activity-was observed in doses up to 2.56 g/kg ip and 1.28 g/kg iv.
• Identification of diamine linkers with differing reactivity and their application in the synthesis of melamine dendrimers
  作者：Karlos X. Moreno、Eric E. Simanek

  DOI：10.1016/j.tetlet.2007.12.056

  日期：2008.2

  Diamine linkers for the synthesis of dendrimers based on melamine were identified using competition reactions. The relative reactivity of the surveyed cyclic monoamines varies by 40 times, expanding the previously identified series to an overall relative reactivity range of 320 times. Azetidine is 40 times more reactive than the cyclic, nine-membered ring (C8H17N), and 320 times more reactive than benzylamine. Reactivity differences are attributed to pK(a), values and sterics. Diamines incorporating these groups are useful linkers that can be employed in dendrimer synthesis. Specifically, the nucleophilicity of the individual amine groups comprising 3-aminoazetidine, 3-aminopyrrolidine, and 4-aminopiperidine varies by 100 times, 70 times, and 20 times, respectively. These linkers are incorporated into a generation three dendrimer. (C) 2008 Elsevier Ltd. All rights reserved.